Sclerotigenin
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| Category | Bioactive by-products |
| Catalog number | BBF-05257 |
| CAS | 65641-84-1 |
| Molecular Weight | 277.28 |
| Molecular Formula | C16H11N3O2 |
| Purity | ≥95% |
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Description
Sclerotigenin is a natural benzodiazepine originally isolated from Penicillium sclerotigenum that acts as an insect growth regulator and has an anti-insectan activity against the caterpillar, Helicoverpa zea.
Specification
| Synonyms | 6,7-dihydro-5H,13H-quinazolino[3,2-a][1,4]benzodiazepine-5,13-dione; (±)-Sclerotigenin; 6,7-dihydro-6,8,13a-triaza-benzo[3,4]cyclohepta[1,2-b]naphthalene-5,13-dione; 6,7-dihydrobenzo[6,7][1,4]diazepino[2,1-b]quinazoline-5,13-dione |
| Storage | Store at -20°C |
| IUPAC Name | 6,7-dihydroquinazolino[3,2-a][1,4]benzodiazepine-5,13-dione |
| Canonical SMILES | C1C2=NC3=CC=CC=C3C(=O)N2C4=CC=CC=C4C(=O)N1 |
| InChI | InChI=1S/C16H11N3O2/c20-15-11-6-2-4-8-13(11)19-14(9-17-15)18-12-7-3-1-5-10(12)16(19)21/h1-8H,9H2,(H,17,20) |
| InChI Key | NGYKOTTXJAPLPC-UHFFFAOYSA-N |
Properties
| Appearance | Solid |
| Antibiotic Activity Spectrum | Parasites |
| Melting Point | 268-270°C |
| Density | 1.5±0.1 g/cm3 |
| Solubility | Soluble in DMF, DMSO, Ethanol, Methanol |
Reference Reading
1. Efficient syntheses of 2,3-disubstituted natural quinazolinones via iridium catalysis
Jie Fang, Jianguang Zhou Org Biomol Chem. 2012 Mar 28;10(12):2389-91. doi: 10.1039/c2ob07178a. Epub 2012 Feb 15.
Natural products sclerotigenin, pegamine, deoxyvasicinone, mackinazolinone, and rutaecarpine were synthesized. Core quinazolinone structures were constructed via Ir catalysis.
2. Fluorous synthesis of substituted sclerotigenin library
Yimin Lu, Tadamichi Nagashima, Bruhaspathy Miriyala, Joanne Conde, Wei Zhang J Comb Chem. 2010 Jan-Feb;12(1):125-8. doi: 10.1021/cc9001636.
A fluorous linker-assisted synthetic protocol has been developed for preparation of sclerotigenin-type benzodiazepine-quinazolinone library containing 144 analogues. Amide coupling of fluorous trimethoxybenzyl (TMB)-protected amino esters with anthranilic acids followed by base-promoted cyclizations afforded 4-benzodiazepine-2,5-diones. Further derivatization of benzodiazepinediones by reacting with azidobenzoyl chlorides, cyclization, and fluorous linker cleavage afforded the desired compound library. The reaction intermediates were purified by fluorous solid-phase extraction (F-SPE) and final products were further purified by prep-HPLC.
3. Raistrickindole A, an Anti-HCV Oxazinoindole Alkaloid from Penicillium raistrickii IMB17-034
Jiao Li, Yuanyuan Hu, Xiaomeng Hao, Jiali Tan, Fang Li, Xinran Qiao, Shuzhen Chen, Chunling Xiao, Minghua Chen, Zonggen Peng, Maoluo Gan J Nat Prod. 2019 May 24;82(5):1391-1395. doi: 10.1021/acs.jnatprod.9b00259. Epub 2019 Apr 23.
Raistrickindole A (1), a new indole diketopiperazine alkaloid containing an unusual pyrazino[1',2':2,3][1,2]oxazino[6,5- b]indole tetraheterocyclic ring system, a new benzodiazepine derivative, raistrickin (2), and the known haenamindole (3) and sclerotigenin (4) were isolated from the marine-derived fungus Penicillium raistrickii IMB17-034. Their structures were elucidated by extensive spectroscopic analyses and TDDFT calculations of the NMR and ECD data. Compounds 1 and 2 showed inhibitory activities against the hepatitis C virus.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
